Agents for regulating plant growth

ABSTRACT

Agents for regulating plant growth containing an effective amount of at least one cyclohexanone derivative of the formula I ##STR1## where A, X, n, Y, Z and R have the meanings given in the disclosure, or salts of these compounds, and a process for regulating plant growth.

The present invention relates to agents based on cyclohexenone derivatives which regulate the growth of plants, and a process for regulating plant growth.

It is known that certain 2-acyl-3-hydroxycyclohex-2-en-1-ones have a regulatory influence on plant growth (EP-A-123 001 and EP-A-126 713). Attention is also drawn to EP-A-156 773.

We have now found novel agents for regulating plant growth which contain an effective amount of at least one cyclohexenone derivative of the formula ##STR2## where A is alkoxycarbonyl of 2 to 5 carbon atoms, carboxyl, cyano or trifluoromethyl, X is branched or straight-chain alkylene of 1 to 7 carbon atoms or cycloalkylene of 3 to 7 carbon atoms, n is 0 or 1, with the proviso that n is not 0 when A is alkoxycarbonyl or carboxyl, Y is hydrogen or methyl, Z is hydrogen, alkoxycarbonyl of 2 to 5 carbon atoms or cyano, and R is alkyl or alkoxyalkyl, each of up to 4 carbon atoms, cyclopropyl, benzyl, phenylethyl or acyloxyalkyl, each of up to 6 carbon atoms, or one of its agriculturally acceptable salts.

In formula I, A is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, carboxyl, cyano and trifluoromethyl.

X is, for instance, methylene, ethylene, trimethylene, tetramethylene, methylethylene, dimethylpentamethylene, ethyltrimethylene, 1,2-, 1,3- and 1,4-cyclohexylene, and 1,2-cyclopropylene.

Z is, for example, methoxycarbonyl, ethoxycarbonyl, cyano and hydrogen, and R is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, benzyl, phenylethyl, methoxyethyl, acetoxymethyl and propionoxyethyl.

Examples of suitable salts of compounds of the formula I are agriculturally useful salts, such as alkali metal, especially potassium and sodium, salts, alkaline earth metal, especially calcium, magnesium and barium, salts, manganese, copper, zinc and iron salts, and ammonium, phosphonium, sulfonium and sulfoxonium salts, e.g., tetraalkylammonium salts, benzyltrialkylammonium salts, trialkylsulfonium salts and trialkylsulfoxonium salts.

DE-OS 3,440,410 discloses the use of the cyclohexenone derivatives of the formula I as intermediates for the synthesis of herbicides; their manufacture is also described.

Various synthesis routes for cyclohexenone derivatives are also given in the abovementioned European patent applications.

The synthesis of 2-butyryl-3-hydroxy-4-methoxycarbonyl-5-(4-methoxycarbonylbutyl)-cyclohex-2-en-1-one is described below by way of example.

Manufacturing Example

81 parts by weight of 3-butyryloxy-4-methoxycarbonyl-5-(4-methoxycarbonylbutyl)-cyclohex-2-en-1-one and 8 parts by weight of 4-dimethylaminopyridine were dissolved in anhydrous dichloromethane, and the solution was stirred for 48 hours at room temperature. The solution was washed with 10 wt % strength hydrochloric acid and water, and dried over sodium sulfate. The solvent was distilled off under reduced pressure to give 2-butyryl-3-hydroxy-4-methoxycarbonyl-5-(4-methoxycarbonylbutyl)-cyclohex-2-en-1-one as an oil (compound no. 4).

The compounds in the table below for which physical data are given were prepared similarly. The remaining compounds may be obtained in the same way after selection of the appropriate starting materials, and they are expected to have a biological action similar to that of the compounds investigated. Where X is an asymmetrical alkylene radical, the bond on the left in the table is attached to substituent A.

    __________________________________________________________________________     Compound no.                                                                           A          X              n Y     Z      R   Physical                  __________________________________________________________________________                                                          data*                     1       CF.sub.3 1,4-cyclohexylene                                                                               1 H     H     n-propyl                                                                            0.98 (t), 3.0 (t)         2       CF.sub.3 1,4-cyclohexylene                                                                               1 H     H     ethyl                          3       COOCH.sub.3                                                                             --(CH.sub.2).sub.4 --                                                                           1 H     COOCH.sub.3                                                                          butyl                                                                               0.92 (t), 3.69 (s)                                                             4.81 (t)                  4       COOCH.sub.3                                                                             --(CH.sub.2).sub.4 --                                                                           1 H     COOCH.sub.3                                                                          n-propyl                                                                            0.92 (t), 2.95 (t),                                                            3.65 (s)                  5       COOCH.sub.3                                                                             --(CH.sub.2).sub.4 --                                                                           1 H     COOCH.sub.3                                                                          ethyl                                                                               1.17 (t), 2.35 (t),                                                            3.83 (s)                  6       COOCH.sub.3                                                                             --(CH.sub.2).sub.4 --                                                                           1 H     COOCH.sub.3                                                                          methyl                                                                              2.59 (s), 3.68 (s),                                                            3.78 (s)                  7       COOCH.sub.3                                                                             --CH(CH.sub.3)CH.sub.2)--                                                                       1 H     COOCH.sub.3                                                                          ethyl                                                                               1.13 (t), 3.05 (q),                                                            3.7 (s)                   8       COOCH.sub.3                                                                             --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     COOCH.sub.3                                                                          methyl                         9       COOCH.sub.3                                                                             --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     COOCH.sub.3                                                                          n-propyl                                                                            0.93 (t), 3.7 (s),                                                             3.8 (s)                   10      COOC.sub.2 H.sub.5                                                                      --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     COOCH.sub.3                                                                          n-propyl                       11      COOn-C.sub.4 H.sub.9                                                                    --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     COOCH.sub.3                                                                          n-propyl                       12      CN       --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     COOCH.sub.3                                                                          n-propyl                       13      CF.sub.3 --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     COOCH.sub.3                                                                          n-propyl                       14      CN       --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     COOCH.sub.3                                                                          ethyl                          15      COOC.sub.2 H.sub.5                                                                      1,2-cyclopropylene                                                                              1 H     COOCH.sub.3                                                                          n-propyl                       16      COOC.sub.2 H.sub.5                                                                      1,2-cyclopropylene                                                                              1 H     COOCH.sub.3                                                                          ethyl                          17      CF.sub.3                  0 CH.sub.3                                                                             H     n-propyl                                                                            1.05 (t), 1.35 (s),                                                            3.05 (t)                  18      CF.sub.3                  0 CH.sub.3                                                                             H     ethyl                          19      CF.sub.3                  0 CH.sub.3                                                                             COOCH.sub.3                                                                          n-propyl                                                                            1.4 (s), 1.65 (q),                                                             3.8 (s)                   20      CF.sub.3                  0 CH.sub.3                                                                             COOCH.sub.3                                                                          ethyl                          21      COOH                      0 H     COOCH.sub.3                                                                          ethyl                          22      COOH                      0 H     COOCH.sub.3                                                                          n-propyl                       23      --COOCH.sub.3                                                                           --CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3 --                                                      1 H     COOCH.sub.3                                                                          n-propyl                                                                            0.9 (t), 3.6 (s),                                                              3.7 (s)                   24      --COOCH.sub.3                                                                           --CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3 --                                                      1 H     COOCH.sub.3                                                                          ethyl                          25      --COOCH.sub.3                                                                           1,2-cyclopropylene                                                                              1 H     H     methyl                         26      --COOCH.sub.3                                                                           1,2-cyclopropylene                                                                              1 H     H     ethyl                          27      --COOCH.sub.3                                                                           1,2-cyclopropylene                                                                              1 H     H     n-propyl                       28      --COO-nC.sub.4 H.sub.9                                                                  1,2-cyclopropylene                                                                              1 H     H     methyl                         29      --COO-n-C.sub.4 H.sub.9                                                                 1,2-cyclopropylene                                                                              1 H     H     ethyl                          30      --COO-n-C.sub.4 H.sub.9                                                                 1,2-cyclopropylene                                                                              1 H     H     n-propyl                       31      --COO-tert-C.sub.4 H.sub.9                                                              1,2-cyclopropylene                                                                              1 H     H     methyl                         32      --COO-tert-C.sub.4 H.sub.9                                                              1,2-cyclopropylene                                                                              1 H     H     ethyl                          33      --COO-tert-C.sub.4 H.sub.9                                                              1,2-cyclopropylene                                                                              1 H     H     n-propyl                       34      --COOH   1,2-cyclopropylene                                                                              1 H     H     methyl                         35      --COOH   1,2-cyclopropylene                                                                              1 H     H     ethyl                          36      --COOH   1,2-cyclopropylene                                                                              1 H     H     n-propyl                                                                            1.0 (t), 3.0 (t)          37      --CN     1,2-cyclopropylene                                                                              1 H     H     methyl                         38      --CN     1,2-cyclopropylene                                                                              1 H     H     ethyl                          39      --CN     1,2-cyclopropylene                                                                              1 H     H     n-propyl                       40      --COOCH.sub.3                                                                           1,2-cyclohexylene                                                                               1 H     H     methyl                         41      --COOCH.sub.3                                                                           1,2-cyclohexylene                                                                               1 H     H     ethyl                          42      --COOCH.sub.3                                                                           1,2-cyclohexylene                                                                               1 H     H     n-propyl                       43      --COO-n-C.sub.4 H.sub.9                                                                 1,2-cyclohexylene                                                                               1 H     H     methyl                         44      --COO-n-C.sub.4 H.sub.9                                                                 1,2-cyclohexylene                                                                               1 H     H     ethyl                          45      --COO-n-C.sub.4 H.sub.9                                                                 1,2-cyclohexylene                                                                               1 H     H     n-propyl                       46      --COO-tert-C.sub.4 H.sub.9                                                              1,2-cyclohexylene                                                                               1 H     H     methyl                         47      --COO-tert-C.sub.4 H.sub.9                                                              1,2-cyclohexylene                                                                               1 H     H     ethyl                          48      --COO-tert-C.sub.4 H.sub.9                                                              1,2-cyclohexylene                                                                               1 H     H     n-propyl                       49      --COOH   1,2-cyclohexylene                                                                               1 H     H     methyl                         50      --COOH   1,2-cyclohexylene                                                                               1 H     H     ethyl                          51      --COOH   1,2-cyclohexylene                                                                               1 H     H     n-propyl                       52      --CN     1,2-cyclohexylene                                                                               1 H     H     methyl                         53      --CN     1,2-cyclohexylene                                                                               1 H     H     ethyl                          54      --CN     1,2-cyclohexylene                                                                               1 H     H     n-propyl                       55      --COOCH.sub.3                                                                           1,3-cyclohexylene                                                                               1 H     H     methyl                         56      --COOCH.sub.3                                                                           1,3-cyclohexylene                                                                               1 H     H     ethyl                          57      --COOCH.sub.3                                                                           1,3-cyclohexylene                                                                               1 H     H     n-propyl                       58      --COO-n-C.sub.4 H.sub.9                                                                 1,3-cyclohexylene                                                                               1 H     H     methyl                         59      --COO-n-C.sub.4 H.sub.9                                                                 1,3-cyclohexylene                                                                               1 H     H     ethyl                          60      --COO-n-C.sub.4 H.sub.9                                                                 1,3-cyclohexylene                                                                               1 H     H     n-propyl                       61      --COO-tert-C.sub.4 H.sub.9                                                              1,3-cyclohexylene                                                                               1 H     H     methyl                         62      --COO-tert-C.sub.4 H.sub.9                                                              1,3-cyclohexylene                                                                               1 H     H     ethyl                          63      --COO-tert-C.sub.4 H.sub.9                                                              1,3-cyclohexylene                                                                               1 H     H     n-propyl                       64      --COOH   1,3-cyclohexylene                                                                               1 H     H     methyl                         65      --COOH   1,3-cyclohexylene                                                                               1 H     H     ethyl                          66      --COOH   1,3-cyclohexylene                                                                               1 H     H     n-propyl                       67      --CN     1,3-cyclohexylene                                                                               1 H     H     methyl                         68      --CN     1,3-cyclohexylene                                                                               1 H     H     ethyl                          69      --CN     1,3-cyclohexylene                                                                               1 H     H     n-propyl                       70      --COOCH.sub.3                                                                           1,4-cyclohexylene                                                                               1 H     H     methyl                         71      --COOCH.sub.3                                                                           1,4-cyclohexylene                                                                               1 H     H     ethyl                          72      --COOCH.sub.3                                                                           1,4-cyclohexylene                                                                               1 H     H     n-propyl                       73      --COO-n-C.sub.4 H.sub.9                                                                 1,4-cyclohexylene                                                                               1 H     H     methyl                         74      --COO-n-C.sub.4 H.sub.9                                                                 1,4-cyclohexylene                                                                               1 H     H     ethyl                          75      --COO-n-C.sub.4 H.sub.9                                                                 1,4-cyclohexylene                                                                               1 H     H     n-propyl                       76      --COO-tert-C.sub.4 H.sub.9                                                              1,4-cyclohexylene                                                                               1 H     H     methyl                         77      --COO-tert-C.sub.4 H.sub.9                                                              1,4-cyclohexylene                                                                               1 H     H     ethyl                          78      --COO-tert-C.sub.4 H.sub.9                                                              1,4-cyclohexylene                                                                               1 H     H     n-propyl                       79      --COOH   1,4-cyclohexylene                                                                               1 H     H     methyl                         80      --COOH   1,4-cyclohexylene                                                                               1 H     H     ethyl                          81      --COOH   1,4-cyclohexylene                                                                               1 H     H     n-propyl                       82      --CN     1,4-cyclohexylene                                                                               1 H     H     methyl                         83      --CN     1,4-cyclohexylene                                                                               1 H     H     ethyl                          84      --CN     1,4-cyclohexylene                                                                               1 H     H     n-propyl                       85      --COOCH.sub.3                                                                           methylene        1 H     H     methyl                         86      --COOCH.sub.3                                                                           methylene        1 H     H     ethyl                          87      --COOCH.sub.3                                                                           methylene        1 H     H     n-propyl                       88      --COO-n-C.sub.4 H.sub.9                                                                 methylene        1 H     H     methyl                         89      --COO-n-C.sub.4 H.sub.9                                                                 methylene        1 H     H     ethyl                          90      --COO-n-C.sub.4 H.sub.9                                                                 methylene        1 H     H     n-propyl                       91      --COO-tert-C.sub.4 H.sub.9                                                              methylene        1 H     H     methyl                         92      --COO-tert-C.sub.4 H.sub.9                                                              methylene        1 H     H     ethyl                          93      --COO-tert-C.sub.4 H.sub.9                                                              methylene        1 H     H     n-propyl                       94      --COOH   methylene        1 H     H     methyl                         95      --COOH   methylene        1 H     H     ethyl                          96      --COOH   methylene        1 H     H     n-propyl                       97      --CN     methylene        1 H     H     methyl                         98      --CN     methylene        1 H     H     ethyl                          99      --CN     methylene        1 H     H     n-propyl                       100     --COOCH.sub.3                                                                           ethylene         1 H     H     methyl                         101     --COOCH.sub.3                                                                           ethylene         1 H     H     ethyl                          102     --COOCH.sub.3                                                                           ethylene         1 H     H     n-propyl                       103     --COO-n-C.sub.4 H.sub. 9                                                                ethylene         1 H     H     methyl                         104     --COO-n-C.sub.4 H.sub.9                                                                 ethylene         1 H     H     ethyl                          105     --COO-n-C.sub.4 H.sub.9                                                                 ethylene         1 H     H     n-propyl                       106     --COO-tert-C.sub.4 H.sub.9                                                              ethylene         1 H     H     methyl                         107     --COO-tert-C.sub.4 H.sub.9                                                              ethylene         1 H     H     ethyl                          108     --COO-tert-C.sub.4 H.sub.9                                                              ethylene         1 H     H     n-propyl                       109     --COOH   ethylene         1 H     H     methyl                         110     --COOH   ethylene         1 H     H     ethyl                          111     --COOH   ethylene         1 H     H     n-propyl                       112     --CN     ethylene         1 H     H     methyl                         113     --CN     ethylene         1 H     H     ethyl                          114     --CN     ethylene         1 H     H     n-propyl                       115     --COOCH.sub.3                                                                           trimethylene     1 H     H     methyl                         116     --COOCH.sub.3                                                                           trimethylene     1 H     H     ethylene                       117     --COOCH.sub.3                                                                           trimethylene     1 H     H     n-propyl                                                                            0.95 (t), 3.01 (t)                                                             3.69 (s)                  118     --COO-n-C.sub.4 H.sub.9                                                                 trimethylene     1 H     H     methyl                         119     --COO-n-C.sub.4 H.sub.9                                                                 trimethylene     1 H     H     ethyl                          120     --COO-n-C.sub.4 H.sub.9                                                                 trimethylene     1 H     H     n-propyl                       121     --COO-tert-C.sub.4 H.sub.9                                                              trimethylene     1 H     H     methyl                         122     --COO-tert-C.sub.4 H.sub.9                                                              trimethylene     1 H     H     ethyl                          123     --COO-tert-C.sub.4 H.sub.9                                                              trimethylene     1 H     H     n-propyl                       124     --COOH   trimethylene     1 H     H     methyl                         125     --COOH   trimethylene     1 H     H     ethyl                          126     --COOH   trimethylene     1 H     H     n-propyl                                                                            0.89 (t), 2.93 (t),                                                            12.0 (s)                  127     --CN     trimethylene     1 H     H     methyl                         128     --CN     trimethylene     1 H     H     ethyl                          129     --CN     trimethylene     1 H     H     n-propyl                       130     --COOCH.sub.3                                                                           tetramethylene   1 H     H     methyl                                                                              1.42 (m), 2.63 (s),                                                            3.70 (s)                  131     --COOCH.sub.3                                                                           tetramethylene   1 H     H     ethyl                                                                               1.13 (t), 3.05 (q),                                                            3.66 (s)                  132     --COOCH.sub.3                                                                           tetramethylene   1 H     H     n-propyl                                                                            1.02 (t), 3.00 (t),                                                            3.69 (s)                  133     --COO-n-C.sub.4 H.sub.9                                                                 tetramethylene   1 H     H     methyl                                                                              0.93 (t), 2.61 (s),                                                            4.07 (t)                  134     --COO-n-C.sub.4 H.sub.9                                                                 tetramethylene   1 H     H     ethyl                                                                               0.93 (t), 3.05 (q),                                                            4.07 (t)                  135     --COO-n-C.sub.4 H.sub.9                                                                 tetramethylene   1 H     H     n-propyl                                                                            2.32 (t), 3.02 (t),                                                            4.10 (t)                  136     --COO-tert-C.sub.4 H.sub.9                                                              tetramethylene   1 H     H     methyl                         137     --COO-tert-C.sub.4 H.sub.9                                                              tetramethylene   1 H     H     ethyl                          138     --COO-tert-C.sub.4 H.sub.9                                                              tetramethylene   1 H     H     n-propyl                       139     --COOH   tetramethylene   1 H     H     methyl                                                                              1.40 (m), 2.30 (t),                                                            2.59 (s)                  140     --COOH   tetramethylene   1 H     H     ethyl                                                                               97- 98                    141     --COOH   tetramethylene   1 H     H     n-propyl                                                                            64                        142     --CN     tetramethylene   1 H     H     methyl                         143     --CN     tetramethylene   1 H     H     ethyl                          144     --CN     tetramethylene   1 H     H     n-propyl                       145     --COOCH.sub.3                                                                           --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     methyl                         146     --COOCH.sub.3                                                                           --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     ethyl                          147     --COOCH.sub.3                                                                           --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     n-propyl                       148     --COO-n-C.sub.4 H.sub.9                                                                 --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     methyl                         149     --COO-n-C.sub.4 H.sub.9                                                                 --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     ethyl                          150     --COO-n-C.sub.4 H.sub.9                                                                 --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     n-propyl                       151     --COO-tert-C.sub.4 H.sub.9                                                              --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     methyl                         152     --COO-tert-C.sub.4 H.sub.9                                                              --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     ethyl                          153     --COO-tert-C.sub.4 H.sub.9                                                              --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     n-propyl                       154     --COOH   --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     methyl                         155     --COOH   --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     ethyl                          156     --COOH   --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     n-propyl                       157     --CN     --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     methyl                         158     --CN     --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     ethyl                          159     --CN     --CH(CH.sub.3)(CH.sub.2).sub.3 --                                                               1 H     H     n-propyl                       160     --COOCH.sub.3                                                                           --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     H     methyl                         161     --COOCH.sub.3                                                                           --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     H     ethyl                          162     --COOCH.sub.3                                                                           --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     H     n-propyl                       163     --COO-n-C.sub.4 H.sub.9                                                                 --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     H     methyl                         164     --COO-n-C.sub.4 H.sub.9                                                                 --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     H     ethyl                          165     --COO-n-C.sub.4 H.sub.9                                                                 --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     H     n-propyl                       166     --COO-tert-C.sub.4 H.sub.9                                                              --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     H     methyl                         167     --COO-tert-C.sub.4 H.sub.9                                                              --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     H     ethyl                          168     --COO-tert-C.sub.4 H.sub.9                                                              --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     H     n-propyl                       169     --COOH   --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     H     methyl                         170     --COOH   --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     H     ethyl                                                                               1.3 (m), 2.5 (m),                                                              3.1 (q)                   171     --COOH   --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     H     n-propyl                                                                            1.0 (t), 3.0 (q)          172     --CN     --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     H     methyl                         173     --CN     --CH(CH.sub.3)CH.sub. 2 --                                                                      1 H     H     ethyl                          174     --CN     --CH(CH.sub.3)CH.sub.2 --                                                                       1 H     H     n-propyl                       175     --COOCH.sub.3                                                                           --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     H     Methyl                         176     --COOCH.sub.3                                                                           --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     H     ethyl                          177     --COOCH.sub.3                                                                           --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     H     n-propyl                       178     --COO-n-C.sub.4 H.sub.9                                                                 --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     H     methyl                         179     --COO-n-C.sub.4 H.sub.9                                                                 --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     H     ethyl                          180     --COO-n-C.sub.4 H.sub.9                                                                 --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     H     n-propyl                       181     --COO-tert-C.sub.4 H.sub.9                                                              --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     H     methyl                         182     --COO-tert-C.sub.4 H.sub.9                                                              --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     H     ethyl                          183     --COO-tert-C.sub.4 H.sub.9                                                              --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     H     n-propyl                       184     --COOH   --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     H     methyl                         185     --COOH   --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     H     ethyl                          186     --COOH   -- CH.sub.2 CH(CH.sub.3)--                                                                      1 H     H     n-propyl                       187     --CN     --CH.sub.2 CH(CH.sub.3 -)--                                                                     1 H     H     methyl                         188     --CN     --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     H     ethyl                          189     --CN     --CH.sub.2 CH(CH.sub.3)--                                                                       1 H     H     n-propyl                       190     --COOCH.sub.3                                                                           --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     methyl                         191     --COOCH.sub.3                                                                           --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     ethyl                          192     --COOCH.sub.3                                                                           --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     n-propyl                                                                            1.0 (t), 3.1 (t),                                                              3.7 (s)                   193     --COO-n-C.sub.4 H.sub.9                                                                 --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     methyl                         194     --COO-n-C.sub.4 H.sub.9                                                                 --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     ethyl                          195     --COO-n-C.sub.4 H.sub.9                                                                 --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     n-propyl                       196     --COO-tert-C.sub.4 H.sub.9                                                              --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2                                                         1-                                                                               H     H     methyl                         197     --COO-tert-C.sub.4 H.sub.9                                                              --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     ethyl                          198     --COO-tert-C.sub.4 H.sub.9                                                              --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     n-propyl                       199     --COOH   --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     methyl                         200     --COOH   --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     ethyl                          201     --COOH   --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     n-propyl                       202     --CN     --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     methyl                         203     --CN     --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     ethyl                          204     --CN     --(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     n-propyl                       205     --COOCH.sub.3                                                                           --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1-                                                                               H     H     methyl                         206     --COOCH.sub.3                                                                           --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1-                                                                               H     H     ethyl                          207     -- COOCH.sub.3                                                                          --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1-                                                                               H     H     n-propyl                       208     --COO-n-C.sub.4 H.sub.9                                                                 --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1-                                                                               H     H     methyl                         209     --COO-n-C.sub.4 H.sub.9                                                                 --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1-                                                                               H     H     ethyl                          210     --COO-n-C.sub.4 H.sub.9                                                                 --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1-                                                                               H     H     n-propyl                       211     --COO-tert-C.sub.4 H.sub.9                                                              --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1-                                                                               H     H     methyl                         212     --COO-tert-C.sub.4 H.sub.9                                                              --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1 H     H     ethyl                          213     --COO-tert-C.sub.4 H.sub.9                                                              --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1 H     H     n-propyl                       214     --COOH   --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1-                                                                               H     H     methyl                         215     --COOH   --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1-                                                                               H     H     ethyl                          216     --COOH   --CH(CH.sub.3)(CH.sub. 2).sub.2 CH(CH.sub.3)CH.sub.2                                            1-                                                                               H     H     n-propyl                       217     --CN     --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1-                                                                               H     H     methyl                         218     --CN     --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1-                                                                               H     H     ethyl                          219     --CN     --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1-                                                                               H     H     n-propyl                       220     --COOCH.sub.3                                                                           --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                                                        1 H     H     methyl                         221     --COOCH.sub.3                                                                           --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                                                        1 H     H     ethyl                                                                               0.91 (t), 3.06 (q),                                                            3.70 (s)                  222     --COOCH.sub.3                                                                           --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                                                        1 H     H     n-propyl                       223     --COO-n-C.sub.4 H.sub.9                                                                 --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                                                        1 H     H     methyl                         224     --COO-n-C.sub.4 H.sub.9                                                                 --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                                                        1 H     H     ethyl                          225     --COO-n-C.sub.4 H.sub.9                                                                 --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5 )--                                                       1 H     H     n-propyl                       226     --COO-tert-C.sub.4 H.sub.9                                                              --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                                                        1 H     H     methyl                         227     --COO-tert-C.sub.4 H.sub.9                                                              --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                                                        1 H     H     ethyl                          228     --COO-tert-C.sub.4 H.sub.9                                                              --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                                                        1 H     H     n-propyl                       229     --COOH   --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                                                        1 H     H     methyl                         230     --COOH   --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                                                        1 H     H     ethyl                                                                               0.9 (t), 1.1 (t),                                                              3.1 (q)                   231     --COOH   --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                                                        1 H     H     n-propyl                       232     --CN     --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                                                        1 H     H     methyl                         233     --CN     --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                                                        1 H     H     ethyl                          234     --CN     --(CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                                                        1 H     H     n-propyl                       235     --COOH   --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1-                                                                               COOCH.sub.3                                                                          H     n-propyl                       236     --CF.sub.3                                                                              1,3-cyclohexylene                                                                               1 H     H     n-propyl                                                                            0.99 (t), 3.02 (t)        237     --CN     --CH(CH.sub.3)-- 1 H     H     n-propyl                       238     COO-tert-C.sub.4 H.sub.9                                                                --CH(CH.sub.3)-- 1 H     H     n-propyl                                                                            0.95 (t), 1.4 (s),                                                             3.0 (t)                   239     --COOCH.sub.3                                                                           --CH(CH.sub.3)(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2                                             1 H     H     n-propyl                                                                            1.4920                    240     --COOH   --CH(CH.sub.3)-- 1 H     H     ethyl                                                                               2.97 (q), 12.35                                                                (s),                                                                           17.90 (s)                 241     --COO-n-C.sub.4 H.sub.9                                                                 --CH(CH.sub.3)-- 1 H     H     ethyl                                                                               0.95 (t), 3.07 (q),                                                            4.11 (t)                  242     --COOCH.sub.3                                                                           --CH(CH.sub.3)-- 1 H     H     ethyl                                                                               1.13 (t), 1.21 (d),                                                            3.72 (s)                  243     --COOCH.sub.3                                                                           --CH(CH.sub.3)-- 1 H     COOCH.sub.3                                                                          ethyl                                                                               3.03 (m), 3.71 (s),                                                            3.82 (s)                  244     --COOH   --C(CH.sub.3).sub.2 --                                                                          1 H     H     propyl                                                                              0.98 (t), 1.25 (s),                                                            3.01 (t)                  245     --COOCH.sub.3                                                                           --C(CH.sub.3).sub.2 --                                                                          1 H     H     propyl                                                                              0.98 (t), 1.22 (s),                                                            3.72 (s)                  246     --COOH   --(CH.sub.2).sub.2 CH(CH.sub.3)--                                                               1 H     H     ethyl                                                                               0.96 (d), 1.14 (t),                                                            3.05 (q)                  247     --COOCH.sub.3                                                                           --(CH.sub.2).sub.2 CH(CH.sub.3)--                                                               1 H     H     ethyl                                                                               0.91 (d), 3.03 (q),                                                            3.68 (s)                  248     --COOCH.sub.3                                                                           --(CH.sub.2).sub.2 CH(CH.sub.3)--                                                               1 H     H     propyl                                                                              0.95 (m), 3.00 (t),                                                            3.70 (s)                  249     --COOCH.sub.3                                                                           --(CH.sub.2).sub.2 CH(CH.sub.3)--                                                               1 H     COOCH.sub.3                                                                          propyl                                                                              0.94 (m), 2.98 (t),                                                            3.68 (s)                  250     --COOH   --(CH.sub.2).sub.4 --                                                                           1 H     H     butyl                                                                               0.92 (t), 2.37 (t),                                                            3.02 (t)                  251     --COO-n-C.sub.4 H.sub.9                                                                 --(CH.sub.2 ).sub.4 --                                                                          1 H     H     butyl                                                                               0.95 (m), 3.01 (t),                                                            4.09 (t)                  252     --COOCH.sub.3                                                                           --(CH.sub.2).sub.4 --                                                                           1 H     H     butyl                                                                               0.95 (t), 3.02 (t),                                                            3.72 (s)                  253     --COOH   --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     ethyl                                                                               0.89 (d), 1.17 (t),                                                            3.04 (q)                  254     --COOH   --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     butyl                                                                               0.92 (m), 2.32 (t),                                                            3.01 (t)                  255     --COOCH.sub.3                                                                           --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     ethyl                                                                               0.90 (d), 3.05 (q),                                                            3.67 (s)                  256     --COOCH.sub.3                                                                           --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     butyl                                                                               0.90 (m), 3.02 (t),                                                            3.68 (s)                  257     --COO-n-C.sub.4 H.sub.9                                                                 --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     methyl                                                                              0.90 (m), 2.62 (s),                                                            4.07 (t)                  258     --COOH   --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     methyl                                                                              0.92 (d), 2.33 (t),                                                            2.62 (s)                  259     --COOH   --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     propyl                                                                              0.91 (d), 2.33 (t),                                                            3.02 (t)                  260     --COOCH.sub.3                                                                           --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     methyl                                                                              0.88 (d), 2.61 (s),                                                            3.68 (s)                  261     --COOCH.sub.3                                                                           --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     propyl                                                                              0.89 (d), 3.01 (t),                                                            3.69 (s)                  262     --COO-n-C.sub.4 H.sub.9                                                                 --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     ethyl                                                                               1.18 (t), 3.07 (q),                                                            4.08 (t)                  263     --COO-n-C.sub.4 H.sub.9                                                                 --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     butyl                                                                               2.29 (t), 3.03 (t),                                                            4.08 (t)                  264     --COOCH.sub.3                                                                           --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     COOCH.sub.3                                                                          propyl                                                                              0.90 (m), 3.70 (s),                                                            3.79 (s)                  265     --COOCH.sub.3                                                                           --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     COOCH.sub.3                                                                          methyl                                                                              2.62 (s), 3.67 (s),                                                            3.78 (s)                  266     --COOCH.sub.3                                                                           --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     COOCH.sub.3                                                                          ethyl                                                                               1.12 (t), 3.04 (q),                                                            3.67 (s)                  267     --COOCH.sub.3                                                                           --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     COOCH.sub.3                                                                          butyl                                                                               0.92 (m), 3.68 (s),                                                            3.79 (s)                  268     --COO-n-C.sub.4 H.sub.9                                                                 --(CH.sub.2).sub.2 CH(CH.sub.3)CH.sub.2 --                                                      1 H     H     propyl                                                                              2.28 (t), 3.01 (t),                                                            4.07                      __________________________________________________________________________                                                          (t)                                                Salt of                                               Compound no.             compound no.                                                                          Cation(s)                                      __________________________________________________________________________     269                      141    2 Na.sup.+                                     270                      141    Ca.sup.2+                                      271                      139    2 Na.sup.+                                     269                      141    2 Na.sup.+                                     272                      258    Ca.sup.2+                                      273                      258    2 Na.sup.+                                     274                      140    2 Na.sup.+                                     275                      139    Ca.sup.2+                                      276                      250    2 Na.sup.+                                     277                      253    Ca.sup.2+                                      278                      253    2 Na.sup.+                                     279                      140    2 benzyltrimethylammonium                      280                      258    2 benzyltrimethylammonium                      281                      259    2 Na.sup.+                                     282                      254    2 Na.sup.+                                     283                      253    2 benzyltrimethylammonium                      284                      139    2 benzyltrimethylammonium                      __________________________________________________________________________      *Physical data given are melting point (°C.), refractive index and      .sup.1 HNMR signals (ppm), the abbreviations having the following              meanings: s = singlet, d = doublet, t = triplet, q = quartet, m =              multiplet                                                                

The cyclohexenone derivatives of the formula I may have a variety of influences on practically all plant development stages, and are therefore used as growth regulators.

The active ingredients to be used in accordance with the invention may be applied to the crop either by treating the seed, treating the soil (i.e., via the roots), or--the method particularly preferred--by spraying the leaves.

Because the active ingredients are well tolerated by the crop plants, application rates may vary within a wide range.

When the active ingredients are used to treat seed, active ingredient amounts of from 0.001 to 50 g, preferably from 0.01 to 10 g, per kg of seed are generally required.

When the active ingredients are applied to the soil or foliage, amounts of from 0.01 to 12 kg/ha, preferably from 0.25 to 3 kg/ha, are generally considered to be sufficient.

The agents according to the invention may be applied in the usual formulation forms, e.g. solutions, emulsions, suspensions, powders, dusts, pastes or granules.

The agents according to the invention many, in these application forms, also be mixed and applied with other active ingredients, e.g., herbicides, insecticides, other growth regulators, fungicides and fertilizers. When mixed with other growth regulators, synergistic effects also occur; i.e., the action of the combination product is greater than the effect of the individual components added together.

To determine the growth-regulating properties of the compounds, a culture substrate provided with sufficient nutrients was filled into plastic pots 12.5 cm in diameter, and test plants were grown therein.

In the postemergence application method, the candidate compounds were sprayed onto the plants as aqueous formulations. In other experiments, aqueous formulations were applied to the substrate before emergence of the plants. The growth-regulating action observed was confirmed at the end of the experiment by measuring the growth height. The figures obtained were compared with those for untreated plants.

For example, compound no. 140 exhibits clear growth-retarding properties, inter alia in wheat, barley and rice.

Not only was growth height reduced--the leaves also took on a more intense color. The increased chlorophyll content is indicative of a higher rate of photosynthesis, making for bigger yields.

The bio-regulatory properties of the compounds according to the invention were investigated in various series of tests. The compounds used for comparison purposes were:

    ______________________________________                                         A            Chlormequat chloride                                              B            Ex. no. 13 from EP 0 123 001 A1                                   C            Ex. no. 15 from EP 0 123 001 A1                                   D            Daminozid                                                         E            Mepiquat chloride                                                 ______________________________________                                    

1. Test with seedlings under greenhouse conditions

To determine the growth-regulating properties of the candidate compounds, test plants were grown in soil provided with sufficient nutrients in plastic pots (approx. 12.5 cm in diameter; volume: approx. 500 ml).

The compounds were sprayed as aqueous formulations onto the substrate either on the day of sowing (pre-emergence) or after germination (postemergence). The growth-regulating action observed was confirmed at the end of the experiment by measuring the growth height. The figures obtained were compared with those for untreated plants.

Not only was growth height reduced--the leaves also took on a more intense color. The increased chlorophyll content is indicative of a higher rate of photosynthesis, making for bigger yields.

Experiment 1

Spring barley, Aramir variety

Preemergence (soil) treatment

In this experiment, compounds nos. 130, 131, 134 and 140 had a much stronger influence on growth height than comparative compounds A, B and C, without damaging the seedlings.

Experiment 2

Rice, Nihonbare variety

Postemergence soil treatment

Compound no. 140 proved, in various concentrations, to be much more effective than A or C; A (Cycocel) was completely ineffective.

2. Reduction in stem length and yield improvement in rice

10 rice plants of the Girona variety were cultivated in plastic pots according to Kich-Brauckmann under greenhouse conditions. 4.5 g of a peat substrate provided with sufficient mineral nutrient salts was employed per vessel. The substrate was flooded with water.

When the plants had grown to a height of 21 cm, the candidate compounds were poured onto the substrate as aqueous formulations. This application method is substantially equivalent to the soil-drenching method frequently employed for rice.

Compound 140 reduced the height of the rice plants to a greater degree than comparative compound C. It is to be expected that the tendency of plants to lodge will be less under the influence of compound 140 than under that of C. Further, a significantly improved yield and a more favorable harvest index (ratio of grain yield to straw mass) were achieved with compound 140-- at least at an application rate of 5 mg of active ingredient per vessel. Comparative compound C reduced yield and had a less favorable harvest index.

3. Rice seedling test

Young rice seedlings ("Girona" variety) were cultivated in nutrient solutions containing different concentrations of the active ingredients. After 6 days at 25° C. in continuous light, the active ingredient concentration was determined which reduced lengthwise growth of the second leaf-sheath by 50% (=KI₅₀).

(For details, see W. Rademacher and J. Jung, Z. Acher- und Pflanzenbau, 150, 363"371, 1981).

The figures obtained show that compounds 6, 130, 131, 132, 133, 134, 135, 140, 141, 251, 269, 271, 274, 275, 279, 280 and 284 according to the invention achieve the same effect--at much lower application rates--than comparative compounds A, D and E. 

We claim:
 1. A composition for regulating plant growth containing a solid or liquid carrier and a plant growth regulating amount of at least one cyclohexenone derivative of the formula ##STR3## where A is alkoxycarbonyl of 2 to 5 carbon atoms, carboxyl, cyano or trifluoromethyl, X is branched or straight-chain alkylene of 4 to 7 carbon atoms whereby A and the cyclohexene ring are separated by at least 4 carbon atoms, or cycloalkylene of 3 to 7 carbon atoms, n is 0 or 1, with the proviso that n is not 0 when A is alkoxycarbonyl, cyano or carboxyl, Y is hydrogen or methyl, Z is hydrogen, alkoxycarbonyl of 2 to 5 carbon atoms or cyano, and R is alkyl or alkoxyalkyl, each of up to 4 carbon atoms, cyclopropyl, benzyl or phenylethyl, or one of its agriculturally acceptable salts.
 2. A process for regulating plant growth, wherein at least one cyclohexenone derivative of the formula I as set forth in claim 1 is allowed to act on plants or their biotope.
 3. A composition as defined in claim 1, wherein R is alkyl of 1 to 4 carbon atoms.
 4. A composition as defined in claim 1, wherein n is 1 and X is C₄ -C₇ -alkylene.
 5. A process for regulating plant growth, wherein at least one cyclohexenone derivative as set forth in claim 4 is allowed to act on plants or their biotope. 